things to do in Shelter Island Heights, NY

Enjoy a private fishing outing for new and experienced anglers

Take to the water solo or share a tandem kayak

Share a tandem kayak or paddle on your own

Sail straight into Fishers Island Sound, with room to relax or take the wheel

Sail San Diego at sunset on a private 3-hour cruise

Ride Montauk's coastline and uncover Camp Hero's military history

Pair dinner with ocean breezes and a relaxed evening afloat

Raise the sails or unwind aboard a historic yacht

Fish for blackfish with bait, tackle, and catch cleaning included

Discover the art and coastal inspiration behind Mystic's creative community

Enjoy a private cruise with your own food and drinks

Learn fishing techniques from an experienced crew

Take in local sights from the water

Get on the water with kayak options for every skill level

Build your paddling confidence with your own group

Sail privately in San Diego Bay with drinks and snacks included

3-hour sunset sail on a 40-foot boat with drinks and snacks included

Explore the quieter side of the Hamptons by e-bike

See Montauk's iconic lighthouse up close from the water

Help raise the sails or settle in for a relaxed family outing

Drift over reef structure in search of blackfish

Ride quiet lanes through coastal scenery and the landscapes that inspired artists

Combine fishing with panoramic views from the flybridge

Find your fit with kayak options for new and experienced paddlers